


The Road Trip

by madangelwithabox



Category: Supernatural
Genre: Alternate Universe, M/M, Swearing
Language: English
Status: In-Progress
Published: 2013-11-12
Updated: 2013-11-11
Packaged: 2018-01-01 06:06:31
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 4,637
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1041247
Author URL: https://archiveofourown.org/users/madangelwithabox/pseuds/madangelwithabox
Summary: <blockquote class="userstuff">
              <p>After Sam Winchester finishes his first year of college, his older brother Dean takes him on a road trip. Sam brings along his girlfriend Jess and his best friend Cas -- who Dean strikes up an unlikely friendship with. Their journey is marked by times both good and bad, and shifting relationships.</p>
            </blockquote>





	1. Chapter 1

“So get this, Dean -- I’m planning a road trip for this summer!” Sam Winchester exclaimed excitedly as he burst into the apartment he shared with his older brother. Dean hit the power button on the TV remote and turned to the tall, long-haired college freshman. Sam threw himself down on the couch beside him. 

 Though he got no response, Sam continued to spout information enthusiastically. “Jess is totally down for it, and we think we might even get Cas to consider coming! We wanna make it a kind of cross-country, no real destination thing.”

 Dean couldn’t help but smile at his brother’s enthusiasm. “Why a road trip, dude? Kinda random.” 

 “Because, Dean, most of my other friends road-tripped the summer after they finished high school, and they never shut up about how amazing and fun it was. So I finally snapped today and told Jess that this summer we would definitely be doing one. And since Dad probably wouldn’t have let me do something like that...” Sam trailed off awkwardly. 

 Dean shifted in his seat. The Winchester family situation was a tense one. Their mom had died when they were young; Dean four and Sam just a baby. Since then their dad, John, had been a pretty shit father. Dean could remember the confusion John’s rapid mood swings (often spurred on by alcohol) had caused in the household. Half the time he wouldn’t be home for weeks on end, and the other half he’d be a constant presence, breathing down his sons’ necks and ready to explode if they broke any of his spontaneously created rules. Never sure which John was going to be making an appearance at any given time, Dean had taken to caution -- making sure the house was kept up well and always looking after Sam; making sure he was out of trouble and doing well in school so John would have nothing to yell at him about. Dean had even stuck around home for a few years once he graduated high school, waiting for Sam to graduate as well so he could get him the hell out of dodge. When Sam had been accepted to Stanford in California, Dean had gone with him away from Lawrence, Kansas, and found work as a mechanic and an apartment near the university, which he shared with Sam to make sure his brother wouldn’t have to pay completely for rent or a dorm. Yeah, there was no way Sam could have pulled off a road trip back when he lived with their dad. A dad who had actually gotten _angry_ that Sam was moving so far away for college, instead of being happy his son was following his dream of becoming a lawyer.

 Wanting to avoid an uncomfortable conversation, Dean forced a laugh. He was always happy when Sam was happy, so he decided to throw full enthusiasm into this road trip idea.

 “So who’s car is going to be making this journey?” he questioned. Sam looked down sheepishly.

 “We were, uh, probably gonna take Jess’s Prius, actually...” Dean made a disgusted sound in the back of his throat. 

 “No. There’s no way I’m letting you road trip in a freakin’ Prius. That’s just --” He shook his head, physically ridding himself of the thought. “No way man. We’re taking Baby.”

Sam looked up from the carpet in disbelief. “You’d take the Impala -- your precious Impala -- on a road trip with me and my friends? Oh and by the way, I don’t even remember asking you to come.” he stated sarcastically. Dean shot him a glare. 

 “Shut up, bitch. If you’re gonna do this, you’re gonna do it right. I’m at least gonna make sure my little brother has a proper road-trip experience.”

 “Jerk.” Sam replied to Dean, though his soft tone revealed more affection than his words did. Dean had never gotten over the parent-role he played in Sam’s life, and Sam had always been appreciative of that.

 “Okay, we gotta plan this out better. Your vacation starts in two weeks, so we can leave around then... Rufus loves me so I can take as much time off work as I want -- you said Jess was coming, and you mentioned Cas? That’s the nerdy friend of yours, right?” Dean asked. The only one of Sam’s friend group he’d ever really had a conversation with was Jessica Moore, a Psychology major who Sam had been dating since the second month of school. They were that kind of disgustingly perfect couple that seemed old and married even though they hadn’t even hit their 20’s yet. 

 “Yes, Dean, you know Cas -- you’ve met him at like 3 different parties.” Sam answered.

 Dean did vaguely recall meeting a Cas at some point. He didn’t remember ever seeing more than a fleeting glimpse of him though -- the dude had showed up to a few of Sam’s parties, stood awkwardly in a dark corner for not more than 20 minutes, and then bailed.

 “You sure you want him to come? He seemed a little -- off to me.” Sam smacked his brother’s shoulder. 

 “Shut up, dude. He’s just a little -- antisocial. Shy. You know, the bookish English major type. And anyway, he’s never even been out of California. He _have_ to take him if he agrees to come.”

 “Okay, Sammy, okay. You can bring your freakin’ friend.” Dean grumbled. He was sure it would be fine. He got along great with Jess, and who really cared about Cas? Maybe he’d turn out to be cool, maybe he’d really just be an antisocial freak -- it’s not like it mattered to Dean.


	2. Chapter 2

Dean leaned casually against the door of his black 1967 Chevy Impala. It was about 7 pm on the day they were due to leave for the road trip -- they had decided to leave late in the day and drive through the first night, because Sam had needed to help Jess pack up her dorm. He watched as Jess pulled into the parking lot of his and Sam’s apartment complex, shooting a glare at her Prius and letting his gaze wander over its passengers.

Jess sat in the driver’s seat, her wavy blonde hair pulled back into a messy ponytail. Sam sat beside her, looking like a giant comparatively even while seated. And in the back sat an awkward-looking young guy with messy brown-black hair, who Dean assumed was Cas from the vague memories he had of him. He couldn’t help but suppress a grin as the poor guy scrambled out of the car following a hands-holding Sam and Jess. The dude practically radiated the vibes of a perpetual third-wheel. The trio made their way over to the Impala, lugging a minimal amount of baggage. 

“So you’re our chaperone for this little adventure, right?” Jess smirked up at Dean as Sam slipped his arm around her waist. “Gonna make sure we’re good little girls and boys?” Dean rolled his eyes. 

“Jess, you really are the perfect match for Sam. The two of you seem to share the same inner source of sass.” Jess smiled innocently back up at him, and leaned her head against Sam. Behind her, Cas made his way idly up to the group, looking up into the clear California sky. Dean ignored him and began to speak. 

“Okay, before starting anything here, I need to set some ground rules,” Dean began, patting his car with a hand. “Be very careful in my Baby. Should I find any food spillage and/or stains, the responsible party will be murdered. Make sure -- dude, you listening?” Dean snapped his fingers in front of Cas’s face -- the guy appeared to be daydreaming, still gazing up at the sky. At the sound of Dean’s fingers his eyes snapped down, and Dean couldn’t help but note their startling blue color -- which perfectly matched the button-down shirt he had on -- as their eyes met. There was an awkward beat as they stared at each other, and then Cas blinked several times, clearing his throat and letting his gaze fall to the ground.

“Yeah, sorry. I’m tired... I didn’t get much sleep last night.” Cas spoke in a voice deeper and rougher than Dean would have suspected from his appearance. He cleared his throat as well, unsure why the atmosphere had suddenly become so awkward. 

Dean continued to lay the ground rules for the trip -- for example, he was definitely not letting anyone else drive his Baby. He could sense the trio of college kids gradually growing bored with his speech -- so he dragged it out a bit longer, particularly because he was enjoying watching Jess get more and more fidgety.

“Oh my God, Dean, shut up!” Jess finally burst out loudly, jumping up and down on the ground, her ponytail bouncing. “I want to go!” Dean finally stopped ranting.

“Jess and I are gonna run in real quick, I haven’t packed a bag yet.” Sam nodded towards the apartment building. Dean smirked at him.

“Yeah, you were pretty busy the past few nights there, Sammy.” Sam turned a bright shade of red. 

“I’ve been helping Jess pack up her dorm and stuff, dude!” Dean simply smiled.

“Dean, it’s not Sam’s fault I’ve got him totally whipped enough to help me move furniture all weekend. Give the guy a break.” Jess threw the words at Dean as she grabbed Sam by the hand and dragged him across the parking lot. It was a comical sight, such a small chick leading his moose of a brother around by the hand. Dean shook his head slightly. Jess was definitely a keeper. 

He and Cas now stood alone in the quiet parking lot. Cas loitered awkwardly by the back left door beside Dean, and it remained silent for what felt like a long-ass time. Finally, Dean had to ease the tension so he turned, meeting the blue gaze of the younger man.

“Here, lemme stick your bag in the trunk.” He offered. His voice seemed to break Cas out of his daydreaming, and Dean was offered a small, shy smile as he held out his bag.

Dean grabbed it and threw it in the trunk, the slam of the door as he closed it echoing in the silence of the parking lot. He silently cursed Sam for insisting on bringing this guy along -- he seemed like he’d be a tough one to crack. He leaned against the trunk and started prodding at the messy-haired man. 

“So, Cas... weird name. Short for something? Cassandra?” It was not one of Dean’s finer jokes. Cas looked stoically over at him, though Dean thought he could maybe sense a spark of amusement in his eyes. 

“It’s short for Castiel... which I guess isn’t much less weird. Castiel Novak.” Dean bit back a smile at the odd formality with which Cas introduced himself. It was kind of endearing, despite its weirdness. Interested, he allowed himself a moment to study the young man.

Cas was dressed in a bright blue button-down and a pair of worn-out jeans, the tips of a pair of black converse sticking out from the bottoms. His hair was sticking out wildly like he had just rolled out of bed -- as a matter of fact the rumpled state of his clothing suggested the same, as did the bloodshot quality of his otherwise astonishingly blue eyes.

Dean allowed his gaze to travel down, following the lean yet muscular run of Cas’s body. Hey, he was allowed to admire -- Dean Winchester considered himself very open in the appreciation of the human figure. However, despite Cas’s aesthetically pleasing form, this guy clearly wasn’t his type. He seemed to be a little too much of an antisocial nerd type for Dean’s liking. 

His eyes traveled back up to Cas’s smooth face, and he noticed with an uncomfortable start that the guy had been staring right at him. Dean usually had the decency to at least pretend he wasn’t aware of it when someone was checking him out -- Cas was either being a dick about it or wasn’t used to people checking him out. Judging by the flush that traveled across him face, Dean guessed it was the latter. However, before he could think about it anymore, he heard Sam and Jess returning from the apartment.

“Alright kiddies, stick your bags in the trunk and hop in! Sammy gets shot gun -- shut up Jess, no whining -- he’s gonna start this road trip off right!” As Dean barked instructions, Sam threw his and Jess’s bags in the Impala’s trunk and Cas finally turned away from him and climbed in the back seat, on the left side. Still grumbling, Jess jumped in next to him and Sam got in the front. After making sure the trunk was closed Dean stretched, cracking his back, and then hopped in the driver’s seat. “Let’s get this show on the road!”


	3. Chapter 3

The Impala made its way down the highway, heading east. The plan, which Sam had announced excitedly about 15 minutes into the drive, was to head first to Las Vegas. Dean would drive through the night since they had gotten such a late start, then they would sleep through most of tomorrow in a motel and then enjoy a night out in Vegas.

There was an air of excitement in the car. Dean blasted classic rock, and Sam was so excited to be on the trip that he couldn’t even complain. Jess spent much of the first part of the trip bouncing up and down in her seat and practically climbing over Sam’s seat to get her chin on his shoulder, wrapping her arms around him. Cas, however, remained fairly quiet.

A few times, Dean would glance at him through the rear-view mirror. Cas sat with a fairly blank expression, at times pulling forth a polite smile or nod when Sam or Jess would point something out outside or start babbling about God-knows-what. His head was tilted, looking out the window. Dean couldn’t help but wonder what the guy was thinking -- in fact, he wondered why he was even here. He’d so far shown next to no enthusiasm for the trip. Sam had probably forced him to come... Dean couldn’t help but pity him. He knew the power Sam’s puppy-dog eyes could exude. However, he thought perhaps there was more to the story than that. There was something else to him, something that wasn’t just a lack of desire to be there. There was something almost sad in his eyes, yet his lips curled up almost unnoticeably at the corners into a kind of hidden, placid smile.

“Look at that!” Jess exclaimed, pointing out the window as a field blazed by. Dean rolled his eyes, taking them off of Cas.

“Jess, it’s a freakin’ field full of cows.” He felt Jess’s small hand smack his arm.

“Still, it’s interesting!” she insisted, and Dean just shook his head, laughing at the ridiculously high level of enthusiasm she and Sam were showing for a dull stretch of highway. Still, he was just happy to see Sam enjoying himself. After years of watching Sam suffer at home, it was nice to see him smile. 

***

The car pulled into a truck stop about 2 hours into the drive, since Sam and Jess had been whining about getting snacks since the half-hour mark. At this point, Cas still had yet to utter a word. When Dean pulled to a stop Sam and Jess quickly got out, practically skipping to some vending machines around a corner. Dean got out, stretched, and then peered curiously in the back, where Cas was still sitting. 

“Cas, you can come out. You do know how to work a door handle, right?” Cas shot Dean a dirty look and began to clamber out of the car. 

“Yes, I am aware of how to do that.” Cas settled himself against the Impala beside Dean.

“Oh wow, so you can talk!” Dean teased. Cas turned toward him, his eyebrows pushing together. 

“I’m sorry if my silence makes things awkward. It’s just that I’ve never been far from home, and I’ve certainly never been able to enjoy a trip with a group of friends. It’s just... nice. I’ve been enjoying it.” Dean couldn’t believe how weirdly formal this guy was, but he did feel better knowing that Cas actually wanted to be there. However, he seemed to lack a basic understanding of sarcasm. Finding himself in a kind of weird staring contest with Cas yet again, Dean turned back to the parking lot and searched for a topic of conversation. A few yards off he saw a good one: a short, slightly chubby man with black hair and stubble was wandering aimlessly through the lot. What made it a sight worthy of conversation was that he was dressed to the nines, in a formal suit and everything. Dean chuckled, and hit Cas’s shoulder lightly.

“Check him out, man. That’s what I call dressing for the occasion.” Dean and Cas watched the strange man wander around the lot for a moment.

“Well, though out of place, he appears to at least have a wardrobe that includes something other than plaid -- a concept I’ve noticed Sam, and apparently you,” he said, gesturing to Dean’s outfit, “don’t seem to grasp.” There was a twinkle in Cas’s eyes, and Dean couldn’t help but grin widely. Apparently, the guy did speak sarcasm. He was about to fire back some witty response when the strange man turned toward them sharply, and began to make his way over.

“Shit, he saw us watching.” Dean quickly put a hand over his eyes, trying to make it look like he’d been looking at the sky. Cas turned toward him, smirking slightly.

“You weren’t exactly subtle, Dean. Maybe we should --” Cas was cut off when the man reached them, stood a few feet away, and spoke.

“Hello, boys. Name’s Crowley. I was wondering if you could help a fellow out.” The British accent that came from him fit the attire but was also extremely out of place in this sketchy truck stop. Dean and Cas shot each other semi-concerned looks. The man continued on.

“I’m in need of a ride, and I was wondering if you could help. I need to get to Hell.” The man said this with a completely straight face, and Dean began to cough loudly as Cas’s head tilted almost inhumanly. 

“Excuse me?” Dean asked, trying to control his fit of cough-laughter.

“Hell. Hell, Michigan.” Dean began to laugh loudly at the blank expression on the man’s face, who showed seemingly no awareness at any of his oddity, and shook his head.

“Look, man... we’re not headed there. And even if we were, we don’t take hitchhikers.” The man nodded stoically.

“I understand. I’ll try to find some other way then. I have family there, you see.” With that the man turned and wandered off, oblivious to Dean’s now ringing laughter.

“I hope you find your way to Hell, man!” Dean shouted after him, and even Cas began to laugh. As the man disappeared from view, Sam and Jess came wandering back up to the car.

“What’s up?” Jess asked Dean and Cas, who were still laughing. They paused, locked eyes, and then began to laugh again.

“I don’t even know how to explain, Jess.” Dean replied honestly. “But let’s just get going before we get stuck accompanying some weird-ass hitchhiker to Hell.”

“Okay, but in return for you two sharing your little secret, I want Sam to sit in the back with me!” Dean rolled his eyes at her as she grabbed Sam’s hand and pulled him in the backseat. Cas hesitated and then sat in the passenger’s seat as Dean slid into the car as well. 

Dean turned on the radio and “Highway to Hell” started blasting out of the speakers. He and Cas burst out laughing simultaneously. Sam and Jess shot them inquisitive looks but they were too busy laughing at the bizarre sequence of events to respond. After finally gaining his composure back Dean started driving out of the truck stop. He glanced to his side, and smiled as he locked eyes with Cas, who returned the grin. 

***

Dean continued to find his eyes drawn to Cas several times during the drive. Since the truck stop he’d been a bit more talkative but he continued to gaze out the window most of the time. A few times he seemed to sense he was being watched and would look up into the mirror, and Dean would quickly look away from the inquisitive blue gaze. He couldn’t explain why, but he was intrigued by Cas. Now that he knew a sarcastic, humorous person lurked beneath his shy exterior, he was determined to get to know him more, if only to unearth the mystery. 

By about two in the morning Sam and Jess had both fallen asleep in the backseat of the Impala, tangled up into each other. Cas had his forehead pressed against his window, but Dean could see he was awake -- his bright blue eyes reflected against the glass.

“So, Cas, tell me about yourself.” Dean spoke suddenly, his voice breaking the silence. Cas started, and took his head off the window. Dean glanced over and saw a bright red spot on his forehead, and bit his lip to keep from smiling. Cas was endearing -- kind of reminded Dean of an innocent little puppy.

“What would you want to know?” Cas asked curiously. From the tone of his voice, Dean could tell he was genuinely surprised someone wanted to know anything about him. Cas was clearly not used to having many friends, and Dean could guess from the awkward way he conversed that he didn’t usually talk to people for long. Dean shrugged.

“Dunno. Anything, really. I just need to talk. I’m starting to get sleepy.” Cas turned toward him. 

“I’m not -- I’m not very good at holding a conversation, Dean.” Cas offered up this piece of information softly and hesitantly, studying his hands. “Maybe... maybe you can ask me questions and I can answer?” This gave Dean an idea.

“How about this, Cas: let’s play a little something called the Question Game. I ask a question, you answer honestly. Then you ask a question, and I answer honestly. And so on. Sound interesting?” Cas gave him a small nod. Dean thought for a moment, and then asked the first thing that came to his head. 

“So, what’s your family like? Do you have any brothers, sisters, so forth?” Dean’s voice was quiet in the dark.

“I’m one of 4 kids, actually.” Dean let out a low whistle as Cas continued. “There’s Michael, then me... then Gabriel and Anna. It’s just my dad raising us -- my mom left right after Anna was born, and we haven’t heard from her since. It’s not really a big deal, I hardly even think of her.” Cas was hushed as he thought for a minute. 

“I... I can’t think of anything to ask.” Cas’s voice sounded ridiculously bashful. 

“It can be simple shit, Cas. Like... what’s your favorite color?” Cas’s eyes found his in the darkness. 

“Um... I guess I’ve always been a fan of... green.” They stared at each other for a moment and then Dean focused his attention back on the empty road.

 

“What’s your best memory?” Cas asked suddenly. Dean nodded appreciatively at the question. 

“Well there was this one fourth of July when Sam and I were young... I think Sammy was around 13... Our dad was out of town on one of his long stretches of never coming home, and I saved up money to buy some kick-ass fireworks -- I’m talking awesome fireworks.” Dean hadn’t thought about that night in a long time -- it made him feel happy just bringing it up again. “Anyway, that was an awesome night. One of the few times I just had fun while growing up.” He glanced back over at Cas and saw a faint smile on his face. 

“What’s your worst fear?” As Dean asked the question he watched the smile slowly fade. Cas appeared to think for a moment, and then began to speak in a faltering voice.

“I -- I’m afraid of falling.” Dean shot him an incredulous glance, and Cas continued on, explaining. “Most people would call it a fear of heights. But I figure -- it’s not the height you’re afraid of, it’s the thought of falling.” The car was silent as Dean thought that over.

“Well, that’s certainly a nice way of putting it.” He said after a moment. 

“Being an English major has to count for something! If I’m not eloquent then what’s the point?” Cas replied with false cheerfulness. “What’s your worst fear, if I can reuse the question?” Dean saw Cas yawn out of the corner of his eye as he asked the question.

“I’d have to say -- anything bad happening to Sammy.” Dean spoke honestly. “I’ve spent basically my entire life taking care of him, and I can’t stand the thought of anything... anything hurting him. Especially not now that he’s finally away from John.” Dean swallowed hard and looked in the rear-view mirror at Sam and Jess, who were sleeping peacefully.

“So Cas, how do you know my brother, anyway? And how’d he convince you to come on this trip?” Dean tried for a more light-hearted question, as a heavy tension had begun to build up in the car over the course of the past few turns. He saw Cas shake his head minutely and grin.

“Dean, I believe that is two questions.” Dean couldn’t help but feel a little impressed at Cas’s sarcastic tone. 

“Oh, blow me, Cas.” He noticed out of the corner of his eye with relative glee that Cas’s face turned a bright shade of red at his use of the expression. “They’re related. And besides, I can tell you like answering more than asking.” Cas acknowledged this with a nod. 

“I met him in a class the first semester -- a math Gen Ed. We bonded over our shared lack of prowess in the subject.” He paused, and appeared to be thinking. “And I just happened to be hanging out with him and Jess when Sam first thought of the idea for the road trip. Jess remembered I had mentioned never being out of state before, and kind of insisted I come. I didn’t want to, but then Sam did his puppy-dog-eye thing.” Dean laughed loudly, and saw Sam and Jess stir in the back. He quickly suppressed his laughter.

“I thought it would be something like that.” Cas smiled at Dean.

“Okay, Dean... Why did you want to do this road trip?” Cas asked. 

“Well, I’ve always looked after Sammy. And I feel bad the poor kid never got to do something like this before -- he deserves to experience all the fun crap he missed as a teenager.” Dean was silent for a moment before he added in a softer voice, “And I guess I wanted to experience it too. I -- I’ve always been so busy taking care of Sam I never got to do anything either. So why not kill two birds with one stone, you know?” He glanced over again and stopped talking.

Cas had fallen asleep at some point while Dean was answering, his head nodding against his chest. There was the ghost of a smile on his face and his dark hair was wild. Dean smiled softly to himself, and drove on.

Finally, about 11 or 12 hours after they had left Stanford, the Impala drove into Las Vegas as the sun rose. Dean shot a glance at Cas in the mirror, who was still asleep, and held back a grin. A night in Vegas was sure to loosen the guy up -- this should be fun.

**Author's Note:**

> So this is my first time trying to write a fic longer than 500 words, and I'm mostly doing it for fun, so sorry if it's no good! Also: sorry for the super short exposition in this chapter!


End file.
